| 1. Round | 26/03/2021 | Wexford FC | - | Cabinteely FC | 1:2 |  |
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| 2. Round | 02/04/2021 | Cabinteely FC | - | Cork City | 1:0 | ||||
| 4. Round | 16/04/2021 | UC Dublin | - | Cabinteely FC | 4:1 | ||||
| 5. Round | 23/04/2021 | Cabinteely FC | - | Shelbourne FC | 1:3 | ||||
| 6. Round | 30/04/2021 | Athlone Town | - | Cabinteely FC | 1:2 | ||||
| 8. Round | 14/05/2021 | Bray Wanderers | - | Cabinteely FC | 3:0 | ||||
| 9. Round | 21/05/2021 | Cabinteely FC | - | Treaty United | 2:1 | |
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| 10. Round | 28/05/2021 | Cabinteely FC | - | Wexford FC | 0:2 | |
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| 11. Round | 11/06/2021 | Cork City | - | Cabinteely FC | 0:2 | ||||
| 12. Round | 18/06/2021 | Galway United | - | Cabinteely FC | 1:0 | ||||
| 14. Round | 02/07/2021 | Shelbourne FC | - | Cabinteely FC | 1:0 | ||||
| 16. Round | 17/07/2021 | Cobh Ramblers | - | Cabinteely FC | 1:0 | ||||
| 17. Round | 30/07/2021 | Cabinteely FC | - | Bray Wanderers | 0:3 | ||||
| 18. Round | 06/08/2021 | Treaty United | - | Cabinteely FC | 1:4 | ||||
| 19. Round | 13/08/2021 | Wexford FC | - | Cabinteely FC | 2:1 | |
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| 23. Round | 24/09/2021 | Cabinteely FC | - | Shelbourne FC | 0:2 | ||||
| 24. Round | 01/10/2021 | Athlone Town | - | Cabinteely FC | 2:1 | ||||
| 25. Round | 08/10/2021 | Cabinteely FC | - | Cobh Ramblers | 1:2 |  |
Ireland